List of progestogen esters

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Norethisterone acetate, a widely used progestogen ester and prodrug of norethisterone.
Medroxyprogesterone acetate, a progestogen ester that does not act as a prodrug.

This is a list of progestogen esters, or esters of progestogens.[1][2][3][4][5]

Unlike the case of testosterone and estradiol, progesterone cannot be esterified as it lacks hydroxyl groups, so all progestogen esters, with the exception of esters of 17α-hydroxyprogesterone like hydroxyprogesterone caproate, are esters of progestins (synthetic progestogens) and are non-bioidentical. In addition, whereas all androgen and estrogen esters are prodrugs of the parent compound, only some and not all progestogen esters act as prodrugs. Esters of 17α-hydroxyprogesterone and 19-norprogesterone derivatives like hydroxyprogesterone caproate, medroxyprogesterone acetate, and nomegestrol acetate are active themselves and are not prodrugs, whereas esters of 19-nortestosterone derivatives like norethisterone acetate and norethisterone enanthate are not active themselves and are prodrugs.

Esters of progesterone derivatives[edit]

Esters of 17α-hydroxyprogesterone derivatives[edit]

Marketed[edit]

The following major progestogen esters have been marketed:

And the following minor progestogen esters have been marketed:

The following veterinary-only progestogen esters have also been marketed:

The corticosteroid ester mometasone furoate (Asmanex, Elocom, Elocon, Elosalic, Nasonex), which is a 17α-hydroxyprogesterone derivative, also has very potent progestogenic activity, though it is not used as a progestogen and is instead used exclusively as a corticosteroid.[6]

Never marketed[edit]

Esters of 19-norprogesterone derivatives[edit]

Marketed[edit]

The following progestogen esters have been marketed:

And the following veterinary-only progestogen esters have also been marketed:

Never marketed[edit]

Esters of testosterone derivatives[edit]

Esters of 19-nortestosterone derivatives[edit]

Marketed[edit]

The following progestogen esters have been marketed:

Many 19-nortestosterone androgen esters, such as nandrolone esters like nandrolone decanoate (Deca-Durabolin) and nandrolone phenpropionate (Durabolin), also have potent progestogenic activity.

Never marketed[edit]

Other conjugates of progesterone derivatives[edit]

Ethers of progesterone derivatives[edit]

Marketed[edit]

Although not esters, the following progestogen ethers have been marketed:

  • Pentagestrone acetate (17α-acetoxyprogesterone 3-cyclopentyl enol ether; Gestovis, Gestovister)
  • Quingestrone (progesterone 3-cyclopentyl enol ether; PCPE; Enol-Luteovis; W-3399)

Never marketed[edit]

Cyclic ketals of progesterone derivatives[edit]

Marketed[edit]

Although not esters, the following progestogen cyclic ketals (cyclic acetals) have been marketed:

  • Algestone acetonide (dihydroxyprogesterone acetonide; 16α,17α-isopropylidenedioxyprogesterone; W-3395)
  • Algestone acetophenide (dihydroxyprogesterone acetophenide; DHPA; Neolutin, Droxone, Deladroxone, Decadroxone, Dexadroxate, Bovitrol)
  • Proligestone (14α,17α-propylidenedioxyprogesterone; 14α,17α-dihydroxyprogesterone cyclic acetal with propionaldehyde; Corvinan, Delvosteron)

Oximes of progesterone derivatives[edit]

Never marketed[edit]

Although not esters, the following progestogen oximes have not been marketed:

Other conjugates of testosterone derivatives[edit]

Oximes of 19-nortestosterone derivatives[edit]

Marketed[edit]

Although not esters, the following progestogen oximes have been marketed:

  • Norelgestromin (17α-ethynyl-18-methyl-19-nortestosterone 3-oxime)
  • Norgestimate (17α-ethynyl-18-methyl-19-nortestosterone 3-oxime 17β-acetate)

Never marketed[edit]

See also[edit]

References[edit]

  1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. ISBN 978-1-4757-2085-3. 
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1. 
  3. ^ https://www.drugs.com/drug-class/progestins.html
  4. ^ http://www.micromedexsolutions.com
  5. ^ Sweetman, Sean C., ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. ISBN 978-0-85369-840-1. 
  6. ^ Austin RJ, Maschera B, Walker A, Fairbairn L, Meldrum E, Farrow SN, et al. (2002). "Mometasone furoate is a less specific glucocorticoid than fluticasone propionate". Eur. Respir. J. 20 (6): 1386–92. doi:10.1183/09031936.02.02472001. PMID 12503693.